(1) Field of the Invention
The present invention relates to a process for producing 1,2-epoxy-5,9-cyclododecadiene. Particularly, the present invention relates to a process for producing 1,2-epoxy-5,9-cyclododecadiene by monoepoxidizing 1,5,9-cyclododecatriene with hydrogen peroxide. More particularly, the present invention relates to a process for producing 1,2-epoxy-5,9-cyclododecadiene which has a reactive epoxy group and two carbon-to-carbon double bonds and thus is usable for producing a polymer component of paints or adhesives, and capable of converted to cyclododecanone which can be easily converted, by conventional methods, to lactam compounds, lactone compounds and dibasic carboxylic acids which are important as intermediates of synthetic resins and fibers, for example, polyester and polyamide resins and fibers.
(2) Description of the Related Art
Generally, methods for epoxidizing olefin compounds with hydrogen peroxide are well known. Particularly, the methods for epoxidizing olefin compounds with hydrogen peroxide in the presence of a tungsten compound, a quaternary onium salt and a mineral acid are disclosed in Japanese Examined Patent Publication No. 1-33,471 and No. 3-74,235 and Japanese Unexamined Patent Publication No. 5-213,919. However, none of the above-mentioned Japanese publications teaches a process for producing 1,2-epoxy-5,9-cyclododecadiene by selectively epoxidizing only one carbon-to-carbon double bond of 1,5,9-cyclododecatriene having three carbon-to-carbon double bonds. Also, none of the prior arts disclose an industrial process for producing 1,2-epoxy-5,9-cyclododecadiene from 1,5,9-cyclododecatriene with a high productivity.
Japanese Examined Patent Publication No. 56-104,877 discloses a process for monoepoxidizing 1,5,9-cyclododecatriene to produce 1,2-epoxy-5,9-cyclododecadiene. In this process, 1,5,9-cyclododecatriene is brought into contact with hydrogen peroxide in the presence of a performic acid produced from the reaction of formic acid with hydrogen peroxide in the epoxidation reaction system. This process is disadvantageous in that the yield of the target 1,2-epoxy-5,9-cyclododecadiene based on the amount of the peroxide is low and formic acid, which is very corrosive, must be employed.
Also, Japanese Examined Patent Publication No. 45-13,331 discloses a process for monoepoxidizing 1,5,9-cyclododecatriene with hydrogen peroxide in the presence of a catalyst comprising selenium dioxide, selenious acid or an alkyl selenite ester. This process is disadvantageous in that the necessary reaction time is too long and selenium compounds having a high toxity must be used as a catalyst. Further, Bull. Chem. Soc. Jpn., 42, 1604 (1969) discloses a process for monoepoxidizing 1,5,9-cyclododecatriene with a 90% aqueous hydrogen peroxide solution in the presence of a catalyst consisting of tungstic acid. This process is also disadvantage in that a high concentration hydrogen peroxide, which is very dangerous must be used, the necessary reaction time is long and the yield of the target product is low in comparison with the amount of the peroxide used. Namely, the known prior processes for producing 1,2-epoxy-5,9-cyclododecadiene are unsatisfactory as industrially usable processes.